My thoughts on short term is the first year of the presidency. I agree completely that for significant change to occur there will be needed changes from both sides. I do believe, in addition to greater freedom for family members, Obama will expand the people-to-people exchange policy initiated by the Clinton administration, and all but eliminated under the Bush administration. The number of academics, church groups, students and other groups without commercial purpose travelling to Cuba would increase dramatically. Not exactly a vacation, but an avenue for many to find a way to get there. I know I would try to color myself an academic to make the trip.
In addition the Caribbean countries as a unified group are encouraging Obama to loosen things up for Cuba.
It is a subject I will be watching closely.

Only Congress can end all restrictions on travel, but on January 21 President Obama can use his authority to provide general (no need to apply) licenses for twelve categories of non-tourist travel including family (Cuban American), educational, humanitarian, religious, sports, culture, and ‚Äúsupport for the Cuban people‚ÄĚ.

If he also did away with the special status of Travel Service Providers, any American agent or tour operator could work with local groups to organize non-tourist travel.

While 2/3 of Americans, including of Cuban Americans,and virtually every country in the world, would approve, he is under lots of pressure from the hard liners in Miami not to do even this.